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Potassium Carbonate → 6-chloro-3-nitro-N-(3-piperidin-1-ylpropyl)pyridin-2-amine

HRID 1727035
Notes
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Reaction equation

HRID 1727035 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N:7]1([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[C:20]([Cl:27])[N:19]=1>C1(C)C=CC=CC=1>[Cl:27][C:20]1[N:19]=[C:18]([NH:16][CH2:15][CH2:14][CH2:13][N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19049Piperidine-1-propylamineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 860008436-chloro-3-nitro-N-(3-piperidin-1-ylpropyl)pyridin-2-amineYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

Potassium carbonate (540 mg, 1.5 eq) and 3-piperidino-propylamine (420 mg, 1 eq) are added successively to 2,6-dichloro-3-nitropyridine (500 mg, 1 eq) in solution in toluene (10 ml). After stirring for 2 hours at a temperature of approximately 20° C., the mixture is concentrated under reduced pressure at 40° C. then water (20 ml) and dichloromethane (70 ml) are added. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the solid obtained, by flash chromatography on silica gel (eluent: heptane/ethyl acetate 3:7 to 100% ethyl acetate), produces the expected compound in the form of a yellow solid (473 mg; 61% yield).

Workup

  1. concentrationthe mixture is concentrated under reduced pressure at 40° C.
  2. additionwater (20 ml) and dichloromethane (70 ml) are added
  3. extractionAfter decantation and extractions
  4. washthe combined organic phases are washed with salt water
  5. dry with materialdried over Na2SO4
  6. concentrationthen concentrated under reduced pressure at 40° C
  7. customPurification of the solid
  8. customobtained, by flash chromatography on silica gel (eluent: heptane/ethyl acetate 3:7 to 100% ethyl acetate)

Sources & evidence

ORD record
ord-72809767555d4c14904f18cf70924148
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07495009B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes